Highland Park, Greenwood, IN Real Estate | Highland Park, Greenwood, IN Recently Sold Homes

Experience refined luxury and timeless design in this award-winning custom estate by renowned builder Greg Allen-recipient of the 1998 Home-A-Rama "People's Choice" Award. Perfectly positioned in the heart of Center Grove, this residence blends masterful craftsmanship with sophisticated modern updates to create an unparalleled living experience. Step inside to soaring 14' ceilings, rich architectural detail, and expansive living spaces designed for both grand entertaining and everyday elegance. The newly remodeled kitchen serves as the home's showpiece-featuring premium finishes, generous prep space, and a seamless flow into the main living areas. With 4 spacious bedrooms, each offering walk-in closets, and 4 full baths plus 2 half baths, the home provides exceptional comfort and privacy for family and guests. The fully finished 3,450 sq. ft. walkout basement is its own retreat-complete with a full theater room, private exercise room, and a stylish wet bar. Whether hosting game nights, movie marathons, or weekend gatherings, this space delivers endless opportunity. Outside, your personal resort awaits. Nestled on nearly half an acre, the backyard features a sparkling in-ground pool, multiple outdoor living areas, and lush privacy-creating the ultimate setting for summer entertaining and peaceful relaxation. A rare combination of elegance, quality, and livability, this Center Grove luxury home offers the lifestyle you've been dreaming of-crafted with intention, updated with care, and designed to impress at every turn.

1913 Dockside Drive, Greenwood

Listing courtesy of Keller Williams Indy Metro S. Selling Office: Real Broker, LLC.

$775,000

4 Beds ⋅ 4 Baths

Welcome to desirable Highland Park, where this custom-built home by Ron Wampler offers 4 spacious bedrooms and 3.5 baths. Designed with both comfort and elegance in mind, this property blends timeless details with modern updates. New windows installed in 2025 fill the home with natural light, enhancing the soaring ceilings and beautiful hardwood floors on the main level. The large kitchen features expansive granite counters, 42" tall cabinets, and an oversized island, perfect for entertaining. A bright eating area flows seamlessly to the covered porch, overlooking the beautifully landscaped backyard with a multi-level flower garden. Just off the kitchen, a sunroom with French doors provides flexible space for an office or playroom. The great room features a cozy gas log fireplace, framed by built-in bookshelves that create both warmth and character. The spacious primary suite features a walk in closet, updated bathroom, and access to the covered balcony through double doors. The walk-out basement adds exceptional living space with a workshop/flex space, large family room, wet bar, bedroom, and full bath-ideal for guests or extended family. A huge laundry room is conveniently located on the main floor, while the oversized three-car side-load garage provides ample storage and parking. This home is move-in ready and available for immediate occupancy.

2041 Dockside Drive, Greenwood

Listing courtesy of L.R. Wood Realty LLC. Selling Office: CrestPoint Real Estate.

$950,000

3 Beds ⋅ 4 Baths

Welcome to 1939 Eagle Trace Drive, a custom-built Greg Allen masterpiece perfectly situated on 1.2 acres in the highly sought-after Highland Park neighborhood, within the award-winning Center Grove school district. This 3-bedroom, 3-full bath residence offers the perfect balance of timeless craftsmanship and thoughtful modern updates, creating a home that is as functional as it is impressive. From the moment you step inside, you'll notice the attention to detail. The main level features all-new real hardwood flooring, lending warmth and elegance to the open layout. A dedicated main-level office provides the ideal setting for working from home or managing daily life with ease. The completely updated kitchen is a showpiece, boasting brand new countertops, modern appliances, and a stylish tile backsplash that flows seamlessly into the spacious dining and living areas. The home's lower level is designed for entertaining and relaxation. The fully finished walk-out basement includes a full bar, making it an entertainer's dream, as well as a secure safe room that provides added peace of mind. Whether you're hosting gatherings, watching the big game, or enjoying quiet evenings, this space adapts to fit your lifestyle. Step outside to experience resort-style living in your own backyard. The heated in-ground pool-complete with a brand new liner-offers endless summer enjoyment, while the expansive lot provides both privacy and room to roam. A new roof, new water heater, and water softener add to the home's list of recent upgrades, ensuring years of worry-free living. Practicality meets luxury with the attached 4-car garage, offering abundant storage and workspace. The home's thoughtful layout, high-quality construction, and numerous updates make it a true standout in today's market. 1939 Eagle Trace Drive is more than just a home-it's a lifestyle. With its combination of elegance, comfort, and modern conveniences, this residence offers a rare opportunity to own

1939 Eagle Trace Drive, Greenwood

Listing courtesy of CENTURY 21 Scheetz. Selling Office: Highgarden Real Estate.

$699,900

4 Beds ⋅ 4 Baths

Welcome to Highland Park and this stunning custom-built home, offering 3,874 S.F. of beautifully finished living space. Built in 2000 and meticulously maintained, this property combines timeless craftsmanship built by Ron Wampler with modern comfort. The home features a walkout lower level, perfect for entertaining or relaxing, with sweeping views of the gorgeous lot. Large windows invite in natural light, highlighting the spacious open floor plan. The gourmet kitchen and nook flows seamlessly into the dining and living areas (all new windows $100,000), creating a warm and inviting atmosphere for family gatherings and guests. Upstairs, the primary suite is a true retreat, complete with a spa-like bathroom and generous closet space. Additional bedrooms provide plenty of room for family, guests, or a home office. Outside, you'll enjoy the beautifully landscaped lot, offering privacy, mature trees, and ample space for outdoor living. The walkout design makes it easy to step outside and enjoy evenings on the patio or mornings with a coffee overlooking the yard. Located in one of Greenwood's most desirable neighborhoods, this home combines elegance, function, and location.

2041 Dockside Drive, Greenwood

Listing courtesy of Tomorrow Realty, Inc.. Selling Office: L.R. Wood Realty LLC.

$910,000

5 Beds ⋅ 4 Baths

Live Like You're on Vacation - Every Day! This custom-built ranch with a full basement in the heart of Center Grove's Highland Park neighborhood delivers over 5,400+ sqft of thoughtfully designed bright living space, featuring 5 spacious bedrooms, 3.5 baths, large great room, 2 fireplaces, nice bar in family room in basement with refrig,dishwashwer,wine cooler & TV, a dedicated workout room, and your very own movie theater!! But the real showstopper? Step into your private resort-style backyard featuring a 40x20 heated in-ground pool with a slide, multi-level trex deck with a hot tub, and a beautiful outdoor pavilion with bar seating - perfect for weekend hangouts or impromptu pool parties. Cozy up around the crescent-shaped gas firepit and enjoy a yard surrounded by mature trees for maximum privacy and that peaceful, tucked-away vibe. This one-of-a-kind home is where every day feels like an every day getaway. Welcome Home!

3794 Lomond Court, Greenwood

Listing courtesy of Carpenter, REALTORS®. Selling Office: F.C. Tucker Company.

$790,000

3 Beds ⋅ 3 Baths

This exquisite, custom-built estate in Highland Park embodies luxury living with purpose. Meticulously maintained by its original owners, this masterfully crafted Greg Allen residence showcases exceptional attention to detail. The foyer unfolds into an expansive family room, creating a sense of function and elegance. The heart of the home is the expansive gathering space, seamlessly integrating the kitchen with rich cherry cabinetry, the warmth of a gas fireplace, and views of the private backyard. The primary suite spans the entire south side of the home, with a private entrance to the screened-in porch. The office and formal dining room flank the foyer entrance, providing versatile spaces for productivity and entertaining. The main level also features a conveniently located second bedroom with a private full bathroom. The lower level unfolds into a sprawling retreat, complete with a third bedroom featuring egress window and a full bathroom, an expansive bonus room serving as a fourth private sanctuary, and an expansive walk-out area designed for entertainment and leisure. This incredible space includes a wet bar, game area, movie viewing, and cozy fireside nook. Additional amenities include ample storage. All aspects of this remarkable residence have been thoughtfully designed marrying luxury, comfort, and functionality in perfect harmony.

2025 Caledonian Court, Greenwood

Listing courtesy of Carpenter, REALTORS®. Selling Office: Instate Realty, LLC.

$1,025,000

5 Beds ⋅ 5 Baths

For sale by owner input for comparable purposes only.

2126 Caledonian Court, Greenwood

Listing courtesy of MIBOR REALTOR® Association. Selling Office: CENTURY 21 Scheetz.

$1,500,000

5 Beds ⋅ 6 Baths

Exquisite luxury home situated on a private .68 acre cul-de-sac lot in one of Johnson County's most prestigious communities. Boasting nearly 8,000 total sq ft. this home is second to none and shows TRUE pride of ownership in regards to ( QUALITY, QUALITY, QUALITY ) and has endless interior and exterior amenities rarely seen at any price point in the Center Grove market place including but not limited to: amazing curb appeal with beautiful landscaping, park like backyard with large inground pool, built in hot tub, mammoth covered back porch with fireplace, 18 plus ft ceilings, grilling area, fire pit area, and endless mature trees offering privacy and seclusion throughout the majority of the year. Interior features main floor office, family room, sprawling kitchen equipped with Thermador appliances and loads of cabinets and countertop space, screened in porch, fantastic views with great window package large primary bedroom on main floor features all of the bells and whistles ( sleek walk in shower, stand alone hydro therapy bubble tub, double vanities, large custom closet and much more ) 3 large bedrooms plus bonus room upstairs, basement features tons of windows, full kitchen, workout room, amazing home theatre room, infrared sauna, great room, and much more. If you're looking for TRUE luxury, look no further!!!

2004 Caledonian Court, Greenwood

Listing courtesy of CENTURY 21 Scheetz. Selling Office: F.C. Tucker Company.

$1,377,500

4 Beds ⋅ 7 Baths

Why build when you can buy this COMPLETELY remodeled 4bed, 7 bath beauty in desirable Highland Park!! Totally renovated by Duke Custom Homes. Some updates include; all new Anderson windows, all new exterior doors, 2 New AC units, new gutters, new interior doors & trim along with new interior/exterior lighting. A DREAM kitchen and butlers panty include; All new Custom Amish cabinetry , quartz counter tops, 4 total ovens, 48 in Gas Range-with pro hood, Subzero ref/freezer, Miele Coffee system, 70 bottle double zone wine refrigerator, Ice maker and dual preparing spaces. DeChateaue Hardwood floors through out main level, custom shelving , vaulted ceilings make this open concept warm and inviting. Step outside to a large private yard and outdoor kitchen complete with a blaze grill and fire pit! 18x36 in-ground pool will provide hours of entertainment AND don't forget the added outdoor bathroom. The perfect location in Center Grove school district , walking distance to Dyes Walk Country Club and seconds away shopping/dining- LOCATION! LOCATION! LOCATION! You will NOT want to miss this one!!!

2071 Eagle Trace Drive, Greenwood

Listing courtesy of Keller Williams Indy Metro S. Selling Office: CENTURY 21 Scheetz.

$930,000

4 Beds ⋅ 5 Baths

Behold a masterpiece of design in the heart of Highland Park. This custom-built residence by J Greg Allen Homes offers an unparalleled living experience. Italian marble floors greet you in the stunning foyer with a curved staircase and beautiful beveled glass. Step into the living room and you will find elevated tray ceilings, built in cabinetry and custom lighting. Detailed millwork, 8' doors, and three fireplaces create an ambiance of timeless elegance that travels throughout the home. Entertain with ease. The entertainer's floor plan seamlessly connects living areas, while expansive main and lower-level verandas beckon for indoor-outdoor gatherings. Ample cabinetry, a center island, and a walk in pantry complete a gourmet kitchen. The huge primary suite boasts a separate sitting room with a gas fireplace offering a tranquil escape. A second en suite bedroom on the main level expands possibilities. The lower level features two more large bedrooms, a custom bar with dedicated appliances, a wine room, an exercise room, space for a pool table/games/media, and a unique telephone room/privacy pod. Custom paneling adds warmth to the full wall hearth and its gas fireplace. A three-car garage, with an expanded third overhead door allows for a larger vehicle or other toys. Stamped exterior concrete adds sophistication. The backyard features a pond and waterfall, creating a tranquil escape. New roof and gutters (June 2024) and a dual HVAC system (2017 & 2023) ensure peace of mind. Situated on a quiet cul-de-sac lot within this prestigious 128-home enclave, the home is surrounded by hills, creeks and lakes. This property offers the perfect blend of privacy, community, and refined living. 1916 Caledonian Court is more than just a house, it's a lifestyle!

1916 Caledonian Court, Greenwood

Listing courtesy of Asset One Real Estate Company. Selling Office: F.C. Tucker Company.

$864,600

4 Beds ⋅ 4 Baths

SOPHISTICATED ELEGANCE! Stunning custom home situated in a park-like setting in prestigious Highland Park, a premier Center Grove neighborhood. You will be captivated upon entry into a lovely foyer overlooking the living room with an amazing view! Elaborate custom trim and built-in bookcases add to the living room's magnificence. Open kitchen/hearth room are the perfect combination of chef's delight and cozy relaxation. Gorgeous granite counter tops with 6x6 island and Amish cabinetry with lighting and pull-outs provide charm and functionality. Charming hearth room with gas fireplace offers the perfect space for conversation. Stunning hardwood flooring throughout most of main level. Double tray ceilings in kitchen and primary suite. Many chandeliers throughout. Primary suite boasts dual vanities, garden tub, shower, & 8x10 California-style closet. Lower level offers a family room with wet bar and a bump out area, 2 bedrooms with large walk-in closets, full bath with shower and an 18x65 unfinished storage/mechanical area. 2 furnaces serve the home. Full attic storage available above 3 car garage.

1744 Lanarkshire Drive, Greenwood

Listing courtesy of Indiana Realty Pros, Inc.. Selling Office: CENTURY 21 Scheetz.

$1,170,000

4 Beds ⋅ 5 Baths

Custom Greg Allen Built "Castle on the Corner" Located in the highly sought after Highland Park. Center Grove School district, Boasting over 6000 square feet this house features 4 bedrooms with the primary on the main floor, Primary Bedroom has a dream walk in closet with built in shelves all the way around the room and island in the middle. Massive walk in shower with dual shower heads. Massive complete exercise room with mirrors in basement, Kitchen on the main floor and a kitchen in the basement. Walk-out basement. Dual Islands on the main floor kitchen with a breakfast area. Walk in pantry and Laundry room off the kitchen. New Roof and HVAC units 2023, Dual HVAC systems, one for the upstairs and one for main floor/basement. New Flooring throughout entire home. Close by amenities.

1849 Lanarkshire Drive, Greenwood

Listing courtesy of @ Home Realty. Selling Office: Triple E Realty, LLC.

$852,500

5 Beds ⋅ 5 Baths

No need worry about the big stuff, the seller has updated nearly everything. Located in exclusive Highland Park, this timeless 5 bedroom 4.5 bath home has what you need. The list of updates in the previous 4 years is long which includes Renewal by Anderson windows on the rear, roof, gutter guards, Cambridge quartz kitchen counters, updated cabinets, GE Profile appliances, custom vanities in upper baths, custom tile showers in primary bath and shared bath, HVAC, and a 75 gallon water heater. Work from home in the main floor office with French doors. Relax by the fireplace in the enormous family room. Bedroom 4 has an en suite bath. Bedrooms 2 & 3 share a bath. Other amenities include central vacuum, wired ethernet to all floors, basement theater speakers included, fiber optic to the house, side load garage, battery back up on sump pump and a large storage room in the basement. Enjoy the private back yard which extends into the woods, screen porch, deck and the hot tub.

2140 Caledonian Court, Greenwood

Listing courtesy of Duke Collective, Inc.. Selling Office: CENTURY 21 Scheetz.

$750,000

3 Beds ⋅ 4 Baths

This Custom Ranch is your chance to become a resident of Highland Park Neighborhood, right in the heart of Center Grove! Who is ready to make this just under 6000 sq/ft, split floor plan home your own?! Expansive ceilings, built-in bookcases, plantation shutters, gas fireplace, custom wood cabinets and wood floors are just a few of the upgrades this home boasts. The open floor plan of the family room and kitchen area promoted forward thinking when built by Greg Allen and supports todays lifestyle. Host large dinners in the formal dining room with new built in storage and serving areas. Work from home in the main level, double door home office! Main floor Primary bedroom is oversized and connected to a large en suite bathroom and custom designed walk in closet. Peep the nerve center off the the laundry room to help organize day to day life! A Jack and Jill bathroom connects two wonderful sized bedrooms and finishes out the main level. An extra wide staircase leads you downstairs to an entertainers dream of a full basement with storage galore! Everything you could need including a family room, game room, bonus room, exercise room, a bar w/ full refrigerator and dishwasher, and two mechanical rooms, one that has a second washer & dryer hook up! Two sump pumps, each with a battery backup! New Dual HVAC Systems! Car enthusiasts will fall in love with this 3+ car garage with extra tall ceilings. Rustic, exposed brick and wood wrapped four season room with heating and cooling can be used all year and sits off the kitchen and family room! The back of the home has a concrete patio and larger side yard on east side of home!

3809 Atherton Lane, Greenwood

Listing courtesy of Indiana Realty Pros, Inc.. Selling Office: CENTURY 21 Scheetz.

$939,000

5 Beds ⋅ 4 Baths

This beautiful and timeless built home by Greg Allen Builders is nestled in the heart of Center Grove on a .93 acre lot. The all brick stately home features impressive views of a pond with fountain, creek with rolling hillside and mature landscaping. The concrete stamped driveway, walkway, and front patio are as picturesque as the rear of the property. Exterior features updated and exquisite landscaping, mission paver patio, and architectural roof/gutters. A new pool liner, newer pool pump,and paint. Step inside the home through a glorious beveled glass front door into the grand two-story foyer. Expansive windows provide bright, natural light throughout the home. Upscale interior updates include; white oak solid wood flooring throughout the main level, updated kitchen featuring granite counter-tops, high end appliances, tiled floors, premium window treatments, fresh paint, lighting, carpeting, fixtures, HVAC, Hot Water Heater, and intercom system throughout the home. Primary bedroom suite features rear views of your .93 acre lot, in-ground pool, and entertainment area. The primary bathroom features a vaulted ceiling, marble jetted tub, separate large shower with bench, expansive closet, and double vanity. The upper level features 3 bedrooms, 1 full bath and 2 bonus rooms. One could be a very nice finished area (a studio, exercise room, playroom, in-law suite, craft room). The other room could feature an additional bathroom or large finished closet. The lower level features an entertainment area with billiard table which converts to table tennis. The family room area features wiring for your sound system, access to the impressive patio, in-ground pool, fire pit, creek, and tree-lined property. The spacious 5th bedroom/guest room has access to a full bathroom with tiled floors. The grand bonus room could be finished for a 6th bedroom suite, in-law quarters, media room, kitchen/bar area, additional bathroom or humidified wine cellar.

1800 Lanarkshire Drive, Greenwood

Listing courtesy of Berkshire Hathaway Home. Selling Office: HIVE Realty Group.

$1,180,000

6 Beds ⋅ 6 Baths

This magnificent 7,500 sqft custom-built, ranch-style home in CG presents a walkout basement & an inviting inground pool, offering a luxurious lifestyle. There is room for all w/ 6 beds, an office, & 5.5 baths. 4 beds include ensuite baths & all beds feature spacious walk-in closets. This home is thoughtfully designed, providing abundant storage & showcasing exquisite finishes. The basement is a haven for hobbies & entertainment, equipped w/ home theater equipment, a generous wet bar area, a workshop, & more! Enjoy your days in the expansive backyard, relaxing on the second-story balcony, or sharing meals prepared in the ultimate chef's kitchen. This home truly encompasses every desirable feature, ensuring an exceptional living experience.

1810 Lanarkshire Drive, Greenwood

Listing courtesy of Indiana Realty Pros, Inc.. Selling Office: Keller Williams Indy Metro NE.

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